The Fiction of Virtual Dating

My dating life.

Recently, I’ve taken up a new obsession with fiction. Not so much reading fiction, but mostly, talking about reading fiction. Organizing & researching a list of reading fiction (seriously, I have no idea how anyone reads more than 10 books a year). Even adding reading fiction to my dating app prompts. I even started researching local bookstores not named Amazon or Barnes & Noble to purchase said items for reading fiction.

Hemingway. Grisham. Rowling. Palahnick. French. The list goes on & on, but the ultimate fictional storyteller was staring me in the mirror and I didn’t have to check out Good Reads to explore the author’s themes & motifs. Yes, it was me during a pandemic-friendly virtual date.

OKCupid has seen a whopping 700% increase in virtual dates amongst their users since March. Despite the numbers, it’s a polarizing new norm too – a norm constantly disappointing & disparaging our wildest romantic imaginations. What made my recent virtual date especially interesting was my date was outside of New York City, outside of New York State, the East Coast, even America. She was based in Toronto, Canada. 

I asked myself: was I that desperate for connection?

Rushing over to my white board to analyze my plan for the date led to a roughly .5% chance this virtual date would lead to anything in real life this Millennia. 

After a few back & forth text messages to change the time of the date — it was set for 8pm. I alerted Verizon about the impending International charges.

The moment before you actually send that FaceTime request for a virtual date reminds me of the Marauder’s Map in Harry Potter The Prisoner of Azkaban. A running web of emotions & questions, twists & turns, ebbs & flows to land on what you think may be the proper positioning & mindset for the big moment:

My kitchen has a bright white light and my room has warm Edison bulb lighting. Is it too aggressive to start the call in my room?

I placed the Vanity Fair magazine on my living room coffee table in preparation for the apartment tour. Will this help brand me as sophisticated?


Should I pour my Espolon tequila on-the-rocks now or do it together with the FT date fully up & running?


Most importantly, can I keep my Alo Yoga sweatpants on with a nice black Henley? Or would not wearing jeans be a risky venture into remote lifestyle martyrdom?

I went for it. Ring. Ring. (FaceTime) Ring.

“Oh…hiii you!” She answered abruptly. Immediately, I noticed the “I love you” tattoo under her neck. Her room (or FaceTime’d version of her room), included a beige wall, a light tan bedsheet, and an interesting undersized painting with a few red hearts on the tan wall. She was a vibe – dark engulfing brown eyes, short brown hair, and a calming energy pulsing through the infinitesimal camera on the iPhone X. And no, there was no Maple Leaf symbol on the wall. That was a relief.

“Hey! Hi! Look at you…before I get to the tequila, who is it…you love?” I opined at this glaring tattoo. She answered, cooly, serenely with an anecdote about a deeper spiritual belief I didn’t really understand. It may have been my phone’s audio issues causing the confusion. Or was it the internal pessimism about the situation? Only time would tell.

The conversation & date took off from there and yes, I opted for the tour of my apartment to start things off.

Well, here’s my kitchen. Not bad, right? I love this Ninja smoothie machine. Or blender? What’s it called again? It’s bright in here, sorry about that!

She giggled recognizing some of the eccentricity that has become a polarizing issue with girls on my recent first dates.  Clearly, the concerning inner-monologue around lighting in my apartment was a non-issue as our digital conversation hit the usual bases with the usual responses.

Horoscopes: Yes, I am a Sagittarius. I think it’s because December is a communal month? Do you really believe in all of this? It’s always funny to me how Millennials aren’t “religious” but obsess over the Zodiac.

Dating App History: Yes, I’ve rarely done one of these virtual FaceTime dates. Oh, you too?  Have you ever noticed how everyone who goes on a dating app date says they don’t go on dating app dates often? The stigma…

Travel: My mom brainwashed me as a kid to love Europe so of course, I need to visit there again once this is all over. What’s Toronto like? Yes, I’ve been a couple times. Is Drake’s house that majestic and what part of Toronto is it in?  Canadian men are that entitled?  Never would have guessed that. Look, I can’t speak for all of New York City men, but I…

Edge: What exactly is “edge?” Is it the antagonist of “basic?” Does it mean smoking a joint over a FaceTime date with someone in another country? Attempting French? Insert other hopeless wish of a first date?

The laundry list of topics continued onwards as the clock itched closer to 9pm. It’s always tough on a FaceTime date finding some semblance of spontaneity. There are no other couples at tables near you to commentate over. No servers to impress with small-talk about the Asiago Bruschetta. No subtle Atmospheric Piano scores by Mozart to chime in on unleashing an artistic discussion on music & culture. None of that exists. Only the immovable 5.85 inches of Plasma mobile screen with a backdrop remaining unchanged. Oh, and your roommate playing Fortnight in the background. That too.

Mid-way through the date, it was clear there was a a connection. In person, this first date easily could have led to popping by an art gallery in SoHo, adventuring around Nolita’s Prince Street Pizza, and who knows, even an apartment visit.

What was unclear was what exactly this connection could materialize into. Sure, we were putting ourselves out there, but the fiction of the situation kept growing more pronounced.

What are you even doing, Harrison? You will most likely never see her!


It’s exciting to dream about visiting Toronto & taking a selfie with her outside of Drake’s house, but that fairytale is impossible with the pandemic raging onwards.

Were you hoping for a more scandalous FaceTime? It’s only date #1!

The Nora Ephron fan in me imagined yet another storybook ending (noticing a trend). Canada miraculously opens its borders up to the US in time for the Holiday season. Delta sends me a SKYMILES complementary flight to Toronto. I board, end up in the Emergency Exit row, indulge in a Sun-dried Tomato Ciabatta sandwich with a gin & tonic, land in Toronto and Uber right to her apartment where we indulge in legal THC, and then book a separate flight or trip to either Banff or Vancouver.

Sadly, fiction itched its head out once again. I saw 9pm at the corner of my phone screen vastly approaching as if it this were but another weekly standup Zoom in the calendar. My desk chair started to get even more uncomfortable and yet, I couldn’t possibly dive into my bed at this point during the superficial small-talk. My Ritual Winter Amber candle was beginning to reach its conclusive demise.  Even, my “Funky Hip-Hop” playlist on Spotify couldn’t help but start repeating tunes from 30 minutes before (yes, I use background music during a virtual first date to bring a tiny semblance of normalcy to the situation).

Sure, I had been on a cold streak. But why did I even hope to spend my time on something that held practically no short, medium, or long-term potential to turn into something?  Was I even looking for something in the first place?


As the date reached its inevitable love-less conclusion, I attempted the virtual kiss blow at the end of the date, which she very clearly digitally caught in her hand.

“This was so fun. Let’s do it again sometime,” one of us remarked. It didn’t matter who, for at this point, we both became fans of this inevitably unsatisfying fictional situation.


Even Hemingway or Stein or Rand could never have predicted the fiction of the modern virtual date. Would they have wanted us to invent romantic scenarios like the flight to Toronto to help improve our creative thinking, pressure-less imagination, and memory capabilities? Or would they have taken the form of the realist, the pragmatist, opining for us to only focus on something tangible, something real, something in real life?

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